Jackson Square
Visit Jackson Square
Tours & day trips
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Day trip to Paradise from Miami: Key West Tour with Snorkelling, Open bar
Cruises & boat tours
See all 78 activitiesDay trip to Paradise from Miami: Key West Tour with Snorkelling, Open bar
History & culture
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Key West Conch Tour Train
Private & custom tours
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Dry Tortugas National Park Day Trip by Luxury Private Boat
Adventure & outdoor
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Key West Half-Day Fishing Charter
Popular places to visit
San Carlos Institute - Casa Cuba
You can spend an afternoon exploring the galleries in San Carlos Institute - Casa Cuba during your trip to Key West. Stroll along the area's seaside or experience its lively festivals.
Duval Street
Along one of the southernmost streets in the continental U.S., enjoy a lively area filled with shops, pubs, restaurants and lots of sidewalk acts and vendors.
Oldest House Museum and Garden
With its period décor and vintage documents, South Florida’s oldest house provides an impression of life in the Florida Keys archipelago in the 19th century
Harry S. Truman Little White House
Visit the winter home of President Harry S. Truman to see where some of America’s most important post-war decisions were made.
Audubon House and Tropical Gardens
Visit a house named after famed naturalist John James Audubon. Learn the history of why the house came to be here.
Mel Fisher Maritime Museum
Key West’s definitive maritime museum is an important attraction for anyone wanting to learn about early life in the Keys. Hear stories of slavery, pirates and fishermen.
Top Jackson Square Hotel Deals
Check availability on hotels close to Jackson Square
Southernmost Beach Resort and Guesthouses
La Concha Key West, Autograph Collection
Duval House
The Cabana Inn Key West - Adults Only
Pier House Resort & Spa
Heron House - Adult Only
Pegasus International Hotel
Opal Key Resort & Marina, Key West
Winslow's Bungalows - Key West Historic Inns
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.